Meet the Bourbon Rebel Who Changed American Whiskey
When Trey Zoeller founded Jefferson’s Bourbon in 1997 with his father, Chet, he wasn’t trying to replicate Kentucky’s legacy brands. He was trying to push bourbon somewhere new.
“If I was just doing one thing, I would be completely bored,” said Zoeller. “My friend who’s a master distiller at one of the biggest distilleries says he’s got one job: don’t mess it up. I kind of look at it the opposite way. I think about what I can do to push it.”
That restless curiosity has defined Jefferson’s from the start. Zoeller grew up in Kentucky, where bourbon was so ubiquitous “it was like drinking Coke.” It wasn’t until his father spotted an ad for a barrel of Bushmills Irish whiskey — and Trey joined friends in traveling to Ireland to buy and bottle it — that he saw the potential.
“He paid $13 a bottle when it was bottled up, it was worth $250,” Zoeller recalls. “I thought, wait a second, there’s good margins in this. And if you can buy a barrel from Ireland, why can’t we buy barrels from our friends here in Kentucky?”
Courtesy Jefferson's Bourbon
Armed with his father’s research identifying 2,800 historic distilleries, Zoeller approached the eight still operating in the late 1990s. Seven agreed to sell him whiskey. That outsider’s approach—cherry-picking esoteric lots, blending, and experimenting—set Jefferson’s apart from the start.
Family history runs deep in the brand. Zoeller’s eighth-generation grandmother, Marian McLain, was arrested in 1799 for bootlegging. Jefferson’s recently honored her with a luxury blend bearing her name.
The name “Jefferson’s” itself nods to that history. President George Washington enacted the first federal whiskey tax to pay for the Revolutionary War, a levy that led to McLain’s arrest. Thomas Jefferson later repealed it, making him a symbolic figure in bourbon’s survival.
Innovation has been Jefferson’s hallmark. Zoeller has overseen more than 40 expressions, from double-barreled blends to bourbons aged at sea. His “Ocean” series reenacted historic trade routes, sending barrels around the world to see how salt air and constant motion transformed the spirit. More recently, his “Tropics” project aged bourbon in Singapore’s humid climate, yielding flavors unlike anything from Kentucky. “It was delicious and just so different,” he said. “I think there’s still a lot of room there to bring different flavors out.”
Courtesy Jefferson's Bourbon
Not all experiments succeed. In past interviews, Zoeller has admitted to missteps—like trying to make both a tobacco and Tabasco whiskeys. But he sees failure as part of the process.
“We’ve been doing experiments for so long that I’ve always got a couple hundred different barrels that have different things going on with them. I feel like we peel back the layers of the onion as far as we can if something works, and then we keep peeling them back until it doesn’t work.”
Zoeller’s proudest moment came when he and his father were inducted into the Bourbon Hall of Fame together. “We used to kind of get laughed at,” he recalls. “Turns out we were the tail that wagged the dog, which made others start innovating to catch up.”
His father’s passing last year has made that honor even more meaningful. Asked who he’d most like to share a bourbon with, Zoeller doesn’t hesitate: “Now it’d be with my Dad, because he’s not around.”
He adds that if given the chance, he’d also pour one for Thomas Jefferson himself. Jefferson, he notes, wasn’t a bourbon drinker—he favored wine and brandy—and dismissed bourbon as “for the common man.” Yet Jefferson’s repeal of Washington’s whiskey tax had already shaped Zoeller’s family history, freeing the spirit from a burden that once jailed his ancestor. For Zoeller, sharing a pour with Jefferson would be a full-circle moment: showing the founding father that the whiskey he once saw as rustic has become a global symbol of innovation and heritage.
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Asked how he likes to drink bourbon, Zoeller is straightforward: “I like a big piece of ice, one big cube, and that’s it.” He laughs at the cultural divide he’s noticed: Kentuckians tend to drink bourbon on the rocks, while newcomers from states he visits like Colorado prefer it neat. “I think we grew up drinking everything on ice,” he says.
As for advice to the next generation, Zoeller emphasizes cycles and education. “Trends will continue to change, but one thing’s going to stay constant: bourbon is an unbelievable spirit.”